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Wilson graduated from the University of Saskatchewan with a Bachelor of Science in Civil Engineering and worked for Imperial Oil for three years in the oilfields of Western Canada. In 1985 he graduated from the University of Calgary with an MBA in entrepreneurship and began work as an investment banker with McLeod Young Weir Limited (now Scotia Capital). Wilson co-founded an investment banking advisory firm, Wilson Mackie & Co., in 1991, and in 1993, co-founded FirstEnergy Capital Corp with Rick Grafton, Jim Davidson and N. Murray Edwards. FirstEnergy is a Canadian stock brokerage firm that provides investment-banking services to global participants in the energy sector. With offices in Calgary and London, England, the firm is now 20% owned by the French company Societe Generale.[2] Wilson retired as Chairman of FirstEnergy in 2008.

He invests in the energy, agriculture, real estate, sports, and entertainment industries through his primary holding company, Prairie Merchant Corporation. He is Chairman of Canoe Financial, a privately owned investment management firm focused on Canadian resources.[3] After announcing his departure from Dragons' Den in early 2011, he participated in his own entrepreneurship-themed series, Risky Business.[4] He has a regular column on entrepreneurship in the National Post.[5] His sports interests include ownership in Derby County FC and the Nashville Predators of the National Hockey League. In 2012, he published Redefining Success: Still Making Mistakes through Penguin Books.

Wilson sees corporate social responsibility not as an obligation, but as an opportunity, and believes that strategic philanthropy can create major social and economic benefits.[6] He has shaved his head to support Kids' Cancer Care, and climbed Mount Kilimanjaro to support Alzheimer’s research. He has for many years made annual trips with Youth with a Mission to Mexico to build homes for the poor. He has chronicled his philanthropic perspectives in a series of articles written for Alberta Venture magazine.[6]

Wilson has focused his philanthropic initiatives on his home provinces of Alberta and Saskatchewan. He is a supporter of his alma mater, the University of Saskatchewan, and established the Wilson Centre for Entrepreneurial Excellence there in 2007 to promote entrepreneurship in all colleges at the university.[7] He believes that all students should study a core curriculum of marketing, entrepreneurship and philanthropy starting in elementary school.[8]

Specific events hosted by Wilson have supported prostate cancer, David Foster Foundation[9] Right to Play, Little Warriors, Boomer's Legacy, 777 Run for Sight and Dare to Care and the Veterans' Food Bank. He is helping out the Tomorrow Project, a large research project to discover more about the causes of cancer and related prevention techniques. He is active on funding research into the issue of domestic abuse and has funded the Wilson Centre for Domestic Abuse Studies at the Calgary Counselling Centre.[10] He is a supporter of the Canadian Olympic Swim Team.[11] He also supports the sport of volleyball through the Rally Pointe volleyball centre in Calgary.

Management Alumni Excellence (MAX) Award, University of Calgary, Haskayne School of Business (2003)

International Legacy of Honour, Young Presidents Organization - recognizing the global YPO leader who best exemplifies commitment to excellence in business, community orientation and the ideals of YPO (2004)